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Why 75% of Business Owners Regret Selling

Most business owners celebrate the sale. Most also regret it. In this episode of the Measure Success Podcast, I sit down with Bob Bedritis, founder and managing director of Oswego Private Wealth Management and a certified exit planning advisor, to discuss why nearly 75% of owners regret selling their business, the "wealth gap" that blindsides them, and how to plan the most important act of your life — the one that comes after the business. We cover: • Why nearly 75% of business owners regret the sale — and the wealth gap driving it • The real math of a deal: how $5M on paper becomes $1.5M in your pocket • Why exit planning is really growth planning that should start 5 years out • Making yourself dispensable, not indispensable, so the business runs without you • Your "third act" — building a life of significance after you step away Watch the full episode and ask yourself: if you sold your business tomorrow, would you know what comes next? Connect with Bob: ...
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More Than Money: Building Wealth That Matters with Tyson Ray

What is wealth really for? In this episode of the Measure Success Podcast, Carl sits down with Tyson Ray, CEO and Founding Partner of Form Wealth Advisors, to discuss building wealth that creates a better life. Tyson shares lessons from his career helping business owners, a powerful experience in Israel that reshaped his perspective, and why financial success should always support purpose, relationships, and legacy. Together, they explore retirement, succession planning, giving while you're living, and how business owners can avoid spending their lives chasing more money without enjoying what they've built. Listen now for practical wisdom on wealth, leadership, and measuring success beyond your balance sheet. Connect with Tyson:  LinkedIn https://www.linkedin.com/in/tysonray/   Book Total Succession:  https://totalsuccession.com/   Website https://totalsuccession.com/     Check out this episode!
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Passive Income, AI, and Purpose with Mark Podolsky

What happens after you achieve financial success? In this episode of the Measure Success Podcast, Carl sits down with Mark Podolsky, known as "The Land Geek," to discuss passive income, AI, entrepreneurship, and finding purpose beyond financial success. Mark shares how he transitioned from investment banking to building a successful land investing business and explains why creating systems is the key to gaining both financial freedom and time freedom. Together, Carl and Mark explore how AI is changing the way businesses operate, why leaders should think of AI as an operating system instead of another tool, and why success ultimately comes down to relationships, purpose, and being present. Listen now for practical insights on building wealth, using AI with intention, and measuring success beyond the bottom line. Connect with Mark:  LinkedIn https://www.linkedin.com/in/thelandgeek/   Facebook https://www.facebook.com/thelandgeek   Twitter https://twitter.com/TheLandG...
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Why Entrepreneurs Get Stuck and How to Move

Are you building, coasting, or struggling? In this episode of the Measure Success Podcast, Carl J. Cox welcomes confidence coach Scott Ballard for a conversation about the mindset of today's entrepreneur. Scott explains his "Day 1, Day 2, Day 3" framework and why many business owners become stuck between growth and decline. The discussion covers courage versus confidence, the importance of telling yourself the truth, finding purpose, and taking the next step forward—even when it's uncomfortable. If you're leading a business or navigating change, this episode will challenge how you think about growth and leadership. Listen now and discover what it takes to move back to Day 1. Connect with Scott: Website: https://www.confidencecoach.org LinkedIn: https://www.linkedin.com/pub/scott-ballard/22/504/a32 Instagram: https://Instagram.com/scottconfidence Facebook: https://www.facebook.com/ConfidenceScott YouTube: https://www.youtube.com/user/coach2confidence/ Ch...
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How To Build Relationships That Scale Business

Networking is not about collecting business cards. It is about building relationships that create measurable business growth. In this episode of the Measure Success Podcast, Donnie Boivin, founder of Success Champion Networking, shares how business owners can stop wasting time networking and start building systems that generate real ROI. In this conversation we discuss: • Why most networking groups fail business owners • The difference between introductions and referrals • Building a network that actually creates revenue • How to create strategic relationships that scale • Why business development requires discipline If networking has felt frustrating, this episode offers a different way to think about relationships, sales, and growth. Listen now and start building your championship team. Connect with Donnie:  LinkedIn https://www.linkedin.com/in/donnieboivin/   Facebook https://www.facebook.com/donnie.boivin   Instagram https://www.instagram.com/donnie.boiv...
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What AI Agents Mean for Small Business Growth

AI is moving faster than most businesses realize. In this episode of the Measure Success Podcast, Trent Gillespie, former Amazon executive and CEO of Stellis AI, breaks down what business leaders need to understand about AI agents, automation, and organizational readiness. We discuss: • Why prompts are no longer the main conversation • How AI agents are changing work • What leaders should do to prepare employees for change • Why businesses need visibility in AI search and recommendation systems • How organizations can build AI adoption without overwhelming teams If you think AI is only about saving time, this episode will challenge that assumption. Listen now and start building for your future customer. Connect with Trent:  LinkedIn https://linkedin.com/in/trentgillespie   Website https://trentgillespie.live     Check out this episode!
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How Great Leaders Rebuild After Failure

In this episode of the Measure Success Podcast, Carl J Cox talks with Ryan Hogan , founder and CEO of Talent Harbor , about entrepreneurship, leadership, recruiting, and recovering from failure. Ryan shares the story of building a zombie-themed event company that scaled quickly before collapsing into bankruptcy. He explains the stress, lessons, and rebuilding process that followed. He also discusses launching Hunt A Killer, scaling the business to more than $55M in revenue, and eventually exiting the company. You will learn: • Why great businesses need the right people • How top sales talent changes company growth • What companies miss when hiring salespeople • Why peer groups matter for leaders • How Ryan rebuilt after losing everything If you lead a business, hire talent, or want practical lessons on growth and resilience, this episode is worth your time. Listen now and follow the Measure Success Podcast for more leadership and strategy conversations.   Check out this ...
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